Dyes for thermoplastics

ABSTRACT

Dyes of the formula ##SPC1## 
     Where 
     D is the radical of the diazo component, 
     R is hydrogen, alkyl or aryl, 
     X is hydrogen, cyano or carbamoyl 
     A 1  is A or ##SPC2## 
     And 
     A is hydrogen or an optionally substituted hydrocarbon radical, are eminently suitable for coloring thermoplastic resinous material. Colorations stable to heat and with excellent fastness properties are obtained, the color strength of the dyes being remarkable.

The invention relates to a process for coloring thermoplastics with dyes of the formula I ##SPC3##

wherein A¹ is A or ##SPC4##

D is the radical of a diazo component,

R is hydrogen, alkyl, methylphenyl or phenyl,

X is hydrogen, carbamoyl or cyano,

Z is alkylene, cycloalkylene, aralkylene or arylene, and the alkylene can be interrupted by oxygen, sulfur or N-substituted imino, the

A's independently of one another are hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl, and two

A's together with the nitrogen are a saturated heterocyclic ring of five to seven members.

The radicals D are derived, in particular, from amines of the benzene, benzthiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series.

Examples of substituents of the radicals D of the diazo component are:

In the benzene series: chlorine, bromine, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbomethoxy, carbobutoxy, carbo-β-ethylhexoxy, carbo-β-methoxyethoxy, carbo-β-hydroxyethoxy, optionally N-monosubstituted or N-disubstituted carboxylic acid amide or sulfonamide, methyl, ethyl, butyl, octyl, hexyl, methoxy or ethoxy; N-substituents of the carboxylic acid amides or sulfonamides are, eg., methyl, ethyl, propyl, butyl, β-hydroxyethyl, γ-hydroxypropyl, β-methoxyethyl, γ-methoxypropyl or γ-ethoxypropyl, or groups which form the pyrrolidide, piperidide or morpholide.

In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy.

In the heterocyclic series: chlorine, bromine, nitro, cyano, methyl, C₁₇ H₃₅, ethyl, phenyl, methoxy, ethoxy, methylmercapto, β-carbomethoxyethylmercapto, β-carboethoxyethylmercapto, carbomethoxy, carboethoxy, carbo-β-ethylhexoxy, acetyl, methylsulfonyl or ethylsulfonyl.

Preferred diazo components have at least one substituent, such as methylsulfonyl, phenylsulfonyl, ethylsulfonyl, carboalkoxy, optionally N-substituted carbamoyl and, in particular, cyano, chlorine or bromine.

The radical D can specifically be derived from, eg., the following amines: o-, m- or p-nitroaniline, o-, m- or p-cyanoaniline, 2,4-dicyanoaniline, 2,4,6-tribromoaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methylsulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 2-hexyl-4-nitroaniline, 4-methoxy-2-nitroaniline, 1-amino-2-trifluoromethyl-4-chlorobenzene, 2-chloro-5-aminobenzonitrile, 2-amino-5-chloro-benzonitrile, 1,-amino-2-nitrobenzene-4-sulfonic acid n-butylamide or β-methoxyethylamide, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromoaniline, 2,4-dinitro-6-cyanoaniline, 1-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline, 2-cyano-4-nitro-6-bromoaniline, 1-aminobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 1-amino-2,4-dinitrobenzene-6-carboxylic acid methyl ester or β-methoxyethyl ester, 3,5-dichloroanthranilic acid propyl ester, 3,5-dibromoanthranilic acid β-methoxyethyl ester, N-acetyl-p-phenylenediamine, 4-aminoacetophenone, 4- or 2-aminobenzophenone, 2- and 4-aminodiphenylsulfone, 5-nitroanthranilic acid methyl ester, isobutyl ester, methyldiglycol ester, β-methoxyethyl ester, β-butoxyethyl ester and β-acetoxyethyl ester, 3- or 4-aminophthalic acid β-hydroxyethylamide, 3-amino-6-nitrophthalic acid β-hydroxyethylamide, methylsulfonic acid 2'-aminophenyl ester, 3'-aminophenyl ester or 4'-aminophenyl ester, ethylsulfonic acid 2'-aminophenyl ester, 3'-aminophenyl ester or 4'-aminophenyl ester, butylsulfonic acid 2'-aminophenyl ester, 3'-aminophenyl ester or 4'-aminophenyl ester, benzenesulfonic acid 2'-aminophenyl ester, 3'-aminophenyl ester or 4'-aminophenyl ester, 2-aminoanthraquinone, 1-amino-4-chloroanthraquinone, 2-aminobenzthiazole, 2-amino-benzthiazole-6-carboxylic acid methyl ester, 2-amino-6-methylsulfonylbenzthiazole, 2-amino-6-cyanobenzthiazole, 2-amino-6-nitrobenzthiazole, 5,6- or 6,7-dichloro-2-aminobenzthiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-methylthiazole-5-carboxylic acid ethyl ester, 2-amino-4-methyl-5-acetylthiazole, 2-amino-3-cyano-4-methylthiophene-5-carboxylic acid esters of C₁ - to C₈ -alkanols or C₁ - to C₄ -alkoxyethanol, 2-phenyl-5-amino-1,3,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-β-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole and 2,4-dicyano-3,5-dimethylaniline.

Examples of suitable diazo components of the aminoazobenzene series are: 4-aminoazobenzene, 2',3-dimethyl-4-aminoazobenzene, 3',2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-4',5-dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-chloro-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethoxy-4-aminoazobenzene, 4'-nitro-2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dimethyl-4-aminoazobenzene, 4'-nitro-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene, 3-methoxy-4-aminoazobenzene, 3-chloro-4-aminoazobenzene and 2',3-dichloro-4-aminoazobenzene.

Examples of radicals R other than hydrogen are ethyl, n- or i-propyl, butyl, pentyl, α-ethylpentyl, phenyl or methylphenyl and preferably methyl.

The radicals A can be identical or different. A can be hydrogen or, eg., the following substituents:

alkyl of 1 to 8 carbon atoms, alkyl optionally substituted by hydroxyl, cyano, alkoxy of 1 to 8 carbon atoms, phenoxy, phenoxyethoxy or benzyloxy; cyclohexyl, norbornyl, benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl, phenylbutyl, phenyl optionally substituted by chlorine, methyl, methoxy or ethoxy, polyalkoxyalkyl, hydroxypolyalkoxyalkyl, alkanoyloxyalkyl or alkoxycarbonylalkyl, alkanoyl, aralkanoyl, aroyl, alkylsulfonyl or arylsulfonyl.

Examples of radicals ##EQU1##0 are pyrrolidino, piperidino, morpholino, piperazino, N-methylpiperazino or hexamethyleneimino.

Specific examples of radicals A, other than those mentioned above, are:

1. Unsubstituted or substituted alkyl: ##EQU2## CH₃, C₂ C₅, n- or i-C₃ H₇, n- or i-C₄ H₉, C₆ H₁₃, ##EQU3## CH₂ CH₂ OH, (CH₂)₃ OH, ##EQU4## (CH₂)₄ OH, (CH₂)₆ OH, ##EQU5## (CH₂)₂ O(CH₂)₂ OH, (CH₂)₃ O(CH₂)₄ OH, (CH₂)₃ OC₂ H₄ OH, (CH₂)₂ CN, (CH₂)₅ CN, (CH₂)₆ CN, (CH₂)₇ CN, (CH₂)₂ O(CH₂)₂ CN, (CH₂)₃ O(CH₂)₂ CN, (CH₂)₂ O(CH₂)₂ O(CH₂)₂ CN, (CH₂)₃ OC₂ H₄ OCH₃, (CH₂)₃ OC₂ H₄ OC₂ H₅, (CH₂)₃ O(CH₂)₆ OH, (CH₃)OC₂ H₄ OCH(CH₃)₂, (CH₂)₃ OC₂ H₄ OC₄ H₉, (CH₂)₃ OC₂ H₄ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ OC₂ H₄ C₆ H₅ ##SPC5##

(ch₂)₃ oc₂ h₄ oc₆ h₅ ##EQU6## the corresponding radicals in which two or three groupings -OC₂ H₄ -, ##EQU7## or -OCH-CH₂ - are present, CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅, CH₂ CH₂ OC₃ H₇, CH₂ CH₂ OC₄ H₉, CH₂ CH₂ OC₆ H₅, (CH₂)₃ OCH₃, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, ##EQU8## (CH₂)₃ OC₆ H₁₃, (CH₂)₃ OC₈ H₁₇, (CH₂)₃ O--, (CH₂)₃ OCH₂ C₆ H₅, (CH₂)₃ OC₂ H₄ C₆ H₅, (CH₂)₃ OC₆ H₅, ##EQU9## ##SPC6##

2. Unsubstituted or substituted cycloalkyl and polycycloalkyl: ##SPC7##

3. Aralkyl: ##EQU10## CH₂ C₆ H₅, C₂ H₄ C₆ H₅, ##EQU11## and corresponding radicals with C₆ H₄ CH₃ in place of C₆ H₅.

4. Unsubstituted or substituted phenyl radicals:

C₆ h₅, c₆ h₄ ch₃, c₆ h₅ (ch₃)₂, c₆ h₄ och₃, c₆ h₄ oc₂ h₅, c₆ h₄ och₂ ch₂ oh and C₆ H₄ Cl;

5. CH₂ CH=CH₂, (CH₂)₅ COOCH₃, ##SPC8##

wherein n is 2, 3, 4 or 6, C₂ H₄ OCOCH₃, C₂ H₄ OCHO, C₂ H₄ OCOCH₃, (C₂ H₄ O)₂ COCH₃, (C₂ H₄ O)₂ CHO, (CH₂)₃ OCOH₃ and (CH₂)₃ OCHO.

6. CHO, CH₃ CO, C₂ H₅ CO, C₃ H₇ CO, ##EQU12## C₂ H₅ CO, CH₃ 3C₆ H₄ CO, C₆ H₅ CH₂ CO, C₆ H₅ OCH₂ CO, CH₃ SO₂, C₂ H₅ SO₂, C₆ H₅ SO₂ and CH₃ C₆ H₄ SO₂.

Examples of preferred substituents A are hydrogen, CH₂, C₂ H₅, n- or i-C₃ H₇, n- or i-C₄ H₉, C₆ H₁₃, ##EQU13## ##SPC9## (n= 2, 3, 6), CH₂ CH₂ OCH₃, CH₂ CH₂ OC₂ H₅, CH₂ CH₂ OC₄ H₉, (CH₂)₃ OCH₃, (CH₂)₃ OC₂ H₅, (CH₂)₃ OC₃ H₇, (CH₂)₃ OC₄ H₉, ##SPC10## ##SPC11##

(ch₂)₃ oc₂ h₄ och₃, (ch₂)₃ oc₂ h₄ oc₄ h₉, (ch₂)₃ oc₂ h₄ oc₆ h₅, ##SPC12##

ch₂ c₆ h₅, c₂ h₄ c₆ h₅, ##EQU14## c₆ h₅, c₆ h₄ ch₃ and C₆ H₄ OCH₃.

Examples of radicals Z are alkylene of 2 to 8 carbon atoms, cycloalkylene of 6 to 18 carbon atoms, with 1 to 3 rings, aralkylene of 7 to 10 carbon atoms and arylene of 6 to 15 carbon atoms. Specific examples are: --(CH₂)_(n) -- (n = 2, 3, 4, 6, 8), ##EQU15## --(CH₂)₃ (OC₂ H₄)₂ O(CH₂)₃ --, --(CH₂)₃ O(CH₂)₄ O(CH.sub. 2)₃ --, ##EQU16## ##SPC13## --(CH₂)OCH₂ CH₂ O(CH₂)₃ --, ##SPC14##

Alkylene radicals are particularly preferred, specifically

--(CH₂)p-- (p = 2, 3, 4, 6), as well as --CH₂ --C(CH₃)₂ --CH₂ --, --(CH₂)₃ OC₂ H₄ O(CH₂)₃ -- and --(CH₂)₃ O(CH₂)₄ O(CH₂)₃ --.

The dyes of the formula I may be prepared by reaction of a diazo compound of amines of the formula II

    d--nh.sub.2

with coupling components of the formula III ##SPC15##

wherein R, X, A, and A¹ are as defined above.

The amines are diazotized by conventional methods. The coupling reaction is also carried out by conventional methods, in an aqueous strongly acid to weakly acid medium, if appropriate with solvents added. Sparingly, soluble coupling components are suitably coupled in solvents.

Industrially valuable dyes and dye mixtures are particularly those of the formula Ia ##SPC16##

in which

A¹ is A or ##SPC17##

D¹ is phenyl substituted by chlorine, bromine, trifluoromethyl, methyl, ethyl, methoxy, nitro, cyano, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, C₁ - to C₈ -alkoxycarbonyl, C₁ - to C₄ -alkoxycarbonyl, C₁ - to C₄ -alkoxyethoxycarbonyl, β-(C₁ -C₄ -alkoxyethoxy)-ethoxycarbonyl or N,N-C₁ - to C₄ -dialkylsubstituted sulfamoyl; phenylazophenyl; phenylazophenyl substituted by methyl, chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by nitro, cyano, methylsulfonyl or ethylsulfonyl; benzisothiazolyl; benzisothiazolyl substituted by chlorine, bromine, cyano or nitro; thiazolyl substituted by cyano or nitro; thienyl substituted by methyl, ethyl, propyl, C₁₇ H₃₅, phenyl, cyano, nitro or C₁ - to C₈ -alkoxycarbonyl; or thiadiazolyl substituted by phenyl, methyl, chlorine, bromine, methylmercapto, ethylmercapto or C₁ - to C₄ -alkoxycarbonylethylmercapto;

R¹ is hydrogen or alkyl of 1 to 3 carbon atoms;

X is hydrogen, carbamoyl or cyano;

A is hydrogen; C₁ - to C₈ -alkyl; C₂ - to C₈ -alkyl substituted by hydroxyl, OCHO, OCOCH₃, OCOC₃ H₇, C₂ - to C₄ -hydroxyalkoxy, cyano, C₁ - to C₈ -alkoxy, C₁ - to C₈ -alkoxycarbonyl, phenoxy or phenyl; cyclohexyl, methylcyclohexyl, norbornyl, phenyl, β-hydroxy-β-phenylethyl or (CH₂)₃ (OC₂ H₄)_(m) OT;

m is 1 or 2;

T is C₁ - to C₄ -alkyl, benzyl or phenyl, ##EQU17## is pyrrolidino, piperidino, morpholino, hexamethyleneimino, piperazino, N-methylpiperazino or N-β-hydroxyethylpiperazino and

Z is C₂ - to C₈ -alkylene, ##EQU18## --(CH₂)₃ --N--(CH₂)₃ --, --(CH₂)₃ --OC₂ H₄ -O--(CH₂)₃ --, --(CH₂)₃ --O--(CH₂)₄ O (CH₂)₃ --, ##SPC18##

Particularly important dyes are those of the formula Ib ##SPC19##

in which

B is nitro, cyano, chlorine, bromine, trifluoromethyl, carbomethoxy, carboethoxy, β-methoxycarboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy, phenylazo, chlorophenylazo or dichlorophenylazo,

B¹ is hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, phenylsulfonyl, carboethoxy, methylsulfonyl or ethylsulfonyl,

B² is hydrogen, chlorine, bromine, cyano or methyl and the

A's, independently of one another, are hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl, and

A¹ has the above meanings.

Oxygen-free radicals A, and radicals A containing alkoxy groups, are preferred. Further, the dyes with A¹ = A are preferred as being more easily obtainable.

The corresponding dyes which contain, as the diazo component, benzthiazole, benzisothiazole, thiazole, thiadiazole or thiophene which are unsubstituted or substituted by chlorine, bromine, cyano, methyl, methylmercapto, β-carbomethoxyethylmercapto, β-carboethoxyethylmercapto, carbomethoxy, carboethoxy or acetyl, are also particularly valuable.

Amongst the particularly valuable diazo components, the following may be mentioned specifically: 4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methoxy-4-nitroaniline, 2-amino-5-nitrophenylsulfonic acid dimethylamide, 2-amino-5-nitrophenylsulfonic acid butylamide, 2-amino-5-nitrophenylsulfonic acid β-methoxyethylamide, 2-aminobenzonitrile, 3-chloro-4-aminobenzonitrile, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 3,5-dichloro-2-aminobenzonitrile, 1-amino-2,4-dicyanobenzene, 1-amino-2,4-dicyano-6-chlorobenzene, 2-chloro-4-amino-5-nitrobenzonitrile, 2-amino-3-chloro-5-nitrobenzonitrile, 2-amino-3-bromo-5-nitrobenzonitrile, 2,6-dicyano-4-nitroaniline, 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo---4-nitroaniline, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromoaniline, 2-amino-3,5-dinitrobenzonitrile, 1-amino-4-nitrobenzene-2-methylsulfone, 1-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonylaniline, 1-amino-2-chlorobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 2-amino-diphenylsulfone, 2-amino-5-nitrobenzoic acid esters, 2-amino-3-chloro-5-nitrobenzoic acid esters, 2-amino-3,5-dichlorobenzoic acid esters, 4-aminoazobenzene, 2,3'-dimethyl-4-aminoazobenzene, 2',3-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 3-chloro-4-aminoazobenzene, 2,3-dichloro-4-aminoazobenzene, 2,4-dicyano-3,5-dimethylaniline, 2-trifluoromethylaniline and 2-trifluoromethyl-4-chloroaniline.

Examples of particularly valuable heterocyclic diazo components are 2-amino-4-methylthiazole-5-carboxylic acid ethyl ester, 2-amino-5-phenyl-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-β-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-β-carboethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 2-amino-6-cyanobenzthiazole, 2-amino-3-cyano-4-methylthiophene-5-carboxylic acid esters, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-chloro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzisothiazole, 4-amino-7-nitro-1,2-benzisothiazole, 4-amino-5-bromo-1,2-benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro-1,2-benzisothiazole and 4-aminobenzisothiazole.

The dyes of the formula I are eminently suitable for mass-coloring thermoplastics at temperatures of up to about 300°C. This property of azo dyes of the formula I was unforseeable since azo disperse dyes are usually not as stable to heat as this. In particular, it is surprising that it is especially the azo dyes free from nitro groups which prove very stable to heat on incorporation into molten polyamide. Examples of thermoplastics which can be colored with the above dyes are polystyrene, rigid polyvinyl chloride, polyethylene, polyamides, polyesters, polypropylene, polycarbonates, styrene-butadiene, copolymers are acrylonitrile-butadiene-styrene copolymers. The colorations obtained have excellent fastness properties, especially fastness to light, weathering and plasticizers. The fastness to plasticizers can be modified by selection of the radicals A, whilst the fastness to light depends essentially on D and X.

Compared to dyes of similar hue conventionally used for mass coloring thermoplastics, the dyes of the formula I are of outstanding color strength, which may be up to about 3.5 times that of conventional dyes. Accordingly, the amounts required for coloration are low, being of the order of from 0.01 to about 1% by weight, based on the thermoplastic to be colored. Normally, from 0.03 to 0.05% of dye suffices. As a rule, transparent colorations are obtained, since most of the dyes are soluble in the substrate. Opaque colorations can be obtained by adding, eg., about 1% of titanium dioxide.

The coloration of the thermoplastics is carried out by conventional methods as described, eg., in U.S. Pat. 3,006,882 or British Patent 888,996 (which are incorporated herein by reference).

In the Examples which follow, parts and percentages are by weight, unless stated otherwise.

EXAMPLE 1

22.2 parts of 1.3-propylenediamine are added, in portions, to a mixture of 200 parts by volume of N-methylpyrrolidone, 71 parts of triethylamine and 99 parts of 2,6-dichloro-3-cyano-4-methylpyridine at room temperature. The mixture is then stirred for 5 hours at from 45° to 55°C, diluted with 1,500 parts by volume of water and acidified to pH 1.5 - 2 with hydrochloric acid. The precipitate which separates out is filtered off, washed with water and dried. 97 parts of a product of the formula ##SPC20##

which contains small proportions of the products of the formulae ##SPC21##

are obtained. 11.4 parts of this mixture are stirred, without prior purification, with 30 parts by volume of methoxypropyleneamine for 5 hours at 150°C; the resulting melt is then caused to dissolve in water by acidifying with hydrochloric acid. This gives a solution of the coupling component of the formula ##SPC22##

(which still contains small portions of the coupling components of the formulae ##SPC23##

The mixture obtained is cooled to room temperature and added in portions to a solution of 7 parts of 2-aminobenzonitrile which has been diazotized by conventional methods. The coupling mixture is stirred for 15 minutes at pH 1.5 to 0 and is then buffered to pH 2.5 - 3 with sodium acetate at from 0° to 10°C. The product is filtered off, washed with water and dried; 18 parts of a dye powder are obtained, consisting essentially of the compound of the formula ##SPC24##

with a proportion of the dyes of the formulae ##SPC25##

and ##SPC26##

0.5 part of this dye mixture is thoroughly mixed with 1,000 parts of polystyrene granules or powder by conventional methods, and the mixture is then fused. Hereupon, the dye dissolved; it proves stable in the melt at up to 300°C. On solidification, polystyrene having a strong yellow coloration of excellent fastness to light is obtained. The dye proves equally heat-stable when incorporated into fused polyamide, and the mass-colored polyamide is also very fast to light. The dye is also very suitable for the mass coloring of polypropylene, polyethylene, polyvinyl chloride and polyesters.

EXAMPLE 2

78 parts of 1-amino-2-trifluoromethyl-4-chloro-benzene are dissolved in 400 parts of 96% strength sulfuric acid at from 0 to 20°C. The mixture is cooled to from 0° to 4°C, 130 parts of 45% strength nitrosulfuric acid are added and the batch is stirred at from 0° to 5°C for 3 hours. It is then poured onto 1,200 parts of ice, whilst stirring, and the mixture is stirred for a further 30 minutes and then filtered. After destroying excess nitrous acid, 258 parts of the coupling component of the formula ##SPC27##

(dissolved in dimethylformamide) are added to the diazonium salt solution and the pH of the coupling solution is raised to 2 - 3 by adding sodium hydroxide solution at from 0° to 5°C. When the coupling reaction has ended, the dye which has precipitated, of the formula ##SPC28##

is filtered off, washed with water and dried.

1,000 parts of polystyrene are colored with 0.5 part of this dye, analogously to Example 1; a yellow polystyrene of very good fastness to light is obtained.

The dyes characterized by their substituents in the table which follow can also be used, in the above manner, for mass colorating purposes and give the hues shown in the table.

                                      Table 1                                      __________________________________________________________________________                                          Hue                                       Exam-                                of the mass-                              ple  Z       R.sup.1                                                                            R.sup.2 R.sup.3                                                                            R.sup.4                                                                             R.sup.5                                                                           colored                                   No.                                  polystyrene                               __________________________________________________________________________     3   --CH.sub.2 CH.sub.2 --                                                                  H  (CH.sub.2).sub.2 OCH.sub.3                                                              C.sub.3 H.sub.7                                                                    CN   H  yellow                                    4    "       "  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                           "    "  "                                         5    "       "   "       "   "    Cl "                                         6    "       "  C.sub.2 H.sub.5                                                                         "   "    H  "                                         7    "       "  CH.sub.3 "   "    "  "                                         8    "       "  (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                    "   "    "  "                                         9     "      "  (CH.sub.2).sub.2 OCH.sub.3                                                              "   "    "  "                                         10   "       "   "       "   "    Cl "                                         11   "       "   "       "   CF.sub.3                                                                            H  "                                         12   "       "  (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                           CF.sub.3                                                                            Cl "                                         13   "       "  C.sub.2 H.sub.5                                                                         "   CN   H  "                                         14   "       "   "       "   CF.sub.3                                                                            H  "                                         15   "       "   "       "   "    Cl "                                         16  --CH.sub.2 CH.sub.2 CH.sub.2 --                                                         "  CH.sub.2 CH.sub.2 OH                                                                    "   CN   H  "                                         17   "       "  (CH.sub.2).sub.3 OH                                                                     "   "    "  "                                         18   "       "   "       "   CF.sub.3                                                                            Cl "                                         19   "       "  CH.sub.2 CH.sub.2 OCH.sub.3                                                             "   "    H  "                                         20   "       "  H        "   "    "  "                                         21   "       "  CH.sub.2 CH.sub.2 OCH.sub.3                                                             C.sub.3 H.sub.7                                                                    "    "  "                                         22   "       "  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           COOCH.sub.3                                                                         "  "                                         23   "       "  CH.sub.2 CH.sub.2 OCH.sub.3                                                             "   "    "  "                                         24   "       "   "       "   "    Cl "                                         25   "       "   "       "   CN   "  "                                         26   "       "  (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                    "   CF.sub.3                                                                            H  "                                         27   "       "  CH.sub.2 CH.sub.2 OH                                                                    "   "    "  "                                         28   "       "  C.sub.2 H.sub.5                                                                         "   CN   Cl "                                         29   "       "   "       C.sub.3 H.sub.7                                                                    "    "  "                                         30   "       "   "       "   CF.sub.3                                                                            H  "                                         31   "       "  CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.3                                                                           "    "  "                                         32   "       "   "       "   CN   "  "                                         33   "       "   "       "   COOCH.sub.3                                                                         Cl "                                         34  --(CH.sub.2).sub.3 --                                                                   "  H        CH.sub.3                                                                           CN   H  "                                         35   "       "   "       "   CF.sub.3                                                                            "  "                                         36   "       "  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "   CN   "  "                                         37   "       "   "       H   SO.sub.2 C.sub.6 H.sub.5                                                            "  "                                         38   "       "  CH.sub.2 CH.sub.2 OH                                                                    CH.sub.3                                                                           CN   "  "                                         39   "       "  CH.sub.2 CH.sub.2 OCH.sub.3                                                             "   "    "  "                                         40   "       "   "       C.sub.3 H.sub.7                                                                    "    "  "                                         41   "       "   "       CH.sub.3                                                                           "    Cl "                                         42   "       "  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "   "    H  "                                         43   "       "  CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                       "   "    "  "                                         44   "       "   "       "   "    Cl "                                         45   "       "  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "   "    H  "                                         46   "       "  CH.sub.2 CH.sub.2 OH                                                                    "   "    "  "                                         47   "       "  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "   "    "  "                                             CH.sub.3                                                                       |                                                                 48  --CH.sub.2 --C--CH.sub.2 --                                                             "  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "   "    "  "                                             |                                                                     CH.sub.3                                                                   49   "       "  CH.sub.2 CH.sub.2 OH                                                                    "   "    "  "                                         __________________________________________________________________________

    Exam-                                                                          ple Z      R.sup.1     R.sup.2                                                                           R.sup.3                                                                            R.sup.4                                                                             R.sup.5                                     No.                                                                            __________________________________________________________________________     50  --(CH.sub.2).sub.3 --                                                                (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                  H  CH.sub.3                                                                           CN   H  yellow                                   51  "     (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                        "  "   "    "  "                                        52  "     (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                       "  "   "    "  "                                        53  "     (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4 H.sub.9                                         "  "   "    "  "                                        54  "     C.sub.6 H.sub.5                                                                             "  "   "    "                                                                                 yellow                                   55  "      "           "  "   `    Cl orange                                   56  "     C.sub.6 H.sub.4 CH.sub.3                                                                    "  "   "    H  "                                        57  "                  "  "   "    "  yellow                                             CH.sub.3                                                                       |                                                           58  "     --CH(CH.sub.2).sub.3 C--OH                                                                  "  "   "    "  "                                                  ||                                                           CH.sub.3 CH.sub.3                                                    59  "                  "  "   "    "  "                                        60  "                  "  "   "    "  "                                        61  "     CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "  H   SO.sub.2 C.sub.6 H.sub.5                                                            "  "                                        62  "                  "  CH.sub.3                                                                           CN   "  "                                        63  "     (CH.sub.2).sub. 3 OCHCH.sub.2 OCH.sub.3                                                     "  "   "    "  "                                                  |                                                                     CH.sub.3                                                             64  "     (CH.sub.2).sub.3 OCH.sub.2 CHOC.sub.6 H.sub.5                                               "  "   "    "  "                                                  |                                                                     CH.sub.3                                                             __________________________________________________________________________

                                      Table 2                                      __________________________________________________________________________     No. D            Z                    Hue                                      __________________________________________________________________________     65               --CH.sub.2 --CH.sub.2 --                                                                            yellow                                   66  "            --(CH.sub.2).sub.3 --                                                                               "                                        67  "            --(CH.sub.2).sub.4 --                                                                               "                                        68  "            --(CH.sub.2).sub.6 --                                                                               "                                        69  "            --CH.sub.2 --CH--    "                                                         |                                                                     CH.sub.3                                                      70  "                                 "                                        71  "                                 "                                        72                                    "                                        73  "                                 "                                        74               --CH.sub.2 --CH.sub.2 --                                                                            red                                      75  "            --(CH.sub.2).sub.3 --                                                                               "                                        76  "            --(CH.sub.2).sub.4 --                                                                               "                                        77  "            --(CH.sub. 2).sub.6 --                                                                              "                                        78  "            --(CH.sub.2).sub.8 --                                                                               "                                        79  "            --CH.sub.2 --CH--    "                                                         |                                                                     CH.sub.3                                                      80                                    red                                      81  "            --CH.sub.2 --CH.sub.2 --CH.sub.2 --N--CH.sub.2 --CH.sub.2                       --CH.sub.2 --       red                                                       |                                                                     CH.sub.3                                                      82               --CH.sub.2 --CH.sub.2 --                                                                            orange                                   83  "            --(CH.sub. 2).sub.3 --                                                                              "                                        84  "            --(CH.sub.2).sub.4 --                                                                               "                                        85  "            --(CH.sub.2).sub.6 --                                                                               "                                        86  "            --CH.sub.2 --CH--    "                                                         |                                                                     CH.sub.3                                                      87  "            --(CH.sub.2).sub.3 --N--(CH.sub.2).sub.3 --                                                         "                                                         |                                                                     CH.sub.3                                                      88               --CH.sub.2 --CH.sub. 2 --                                                                           "                                        89  "            --(CH.sub.2).sub.3 --                                                                               "                                        90  "            --(CH.sub.2).sub.4 --                                                                               "                                        91  "            --(CH.sub.2).sub.6 --                                                                               "                                        92  "            --CH.sub.2 --CH--    "                                                         |                                                                     CH.sub. 3                                                     93  "            --(CH.sub.2).sub.3 --N--(CH.sub.2).sub.3 --                                    |                                                                     CH.sub.3                                                      94  "                                 "                                        95               --CH.sub.2 --CH.sub.2 --                                                                            red                                      96  "            --(CH.sub.2).sub.3 --                                                                               "                                        97  "            --(CH.sub.2).sub.4 --                                                                               "                                        98  "            --(CH.sub.2).sub.6 --                                                                               "                                        99               --(CH.sub.2).sub.8 --                                                                               "                                        100 "            --CH.sub.2 --CH--    "                                                         |                                                                     CH.sub.3                                                      101 "                                 "                                                                              bluish                                   102              --(CH.sub.2).sub.3 --                                                                               red                                      103              --(CH.sub.2).sub.4 --                                                                               "                                        __________________________________________________________________________

                                      Table 3                                      __________________________________________________________________________     No. D                 R.sup.1  Z           Hue                                 __________________________________________________________________________     104                  C.sub.2 H.sub.5                                                                       --(CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.                                 2).sub.5       yellow                              105                   "       "            "                                   106                   "       "            red                                     C.sub.2 H.sub.5 OC                                                             ∥                                                                     O                                                                          107   "              (CH.sub.2).sub.3 OCH.sub.3                                                            --(CH.sub.2).sub.3 --                                                                         "                                   108   "               "     --(CH.sub.2).sub.4 --                                                                         "                                   109                   "     --(CH.sub.2).sub.3 --O(CH.sub.2).sub.4                                         O(CH.sub.2).sub.3 --                                                                          yellowish                                                                      red                                 110   "              C.sub.2 H.sub.5                                                                         "            "                                   111    "             C.sub.3 H.sub.7 (n)                                                                   --(CH.sub.2).sub.3 --                                                                         "                                   112   "              C.sub.2 H.sub.5                                                                       --(CH.sub.2).sub.3 --N--(CH.sub.2).sub.3                                                      "-                                                              |                                                                     CH.sub.3                                           113                   "       "            red                                 114   "               "     --(CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.                                 2).sub.3 --    "                                   __________________________________________________________________________

                                      Table 4                                      __________________________________________________________________________     No. D            R       Z          Hue                                        __________________________________________________________________________                     C.sub.3 H.sub.7 (n)                                            115             N∠                                                                              --(CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).su                            b.5          yellow                                                     C.sub.3 H.sub.7 (n)                                            116   "                --(CH.sub.2).sub.2 --                                                                       "                                          117   "          "     --(CH.sub.2).sub.3 --                                                                       "                                          118              "       "          "                                          119              "       "          "                                          120              "       "          "                                          121                      "          "                                          122              "       "          red                                        123              "       "          yellow-                                                                        ish red                                    124              "       "          red                                            ∥                                                                     O                                                                          125             HN--C.sub.2 H.sub.5                                                                     "          yellow-                                                    |          ish red                                    126             NN--H  --(CH.sub.2).sub.3 --                                                                       red                                            CH.sub.3 OC                                                                    ∥                                                                     O                                                                          __________________________________________________________________________

                                      Table 5                                      __________________________________________________________________________     No. D                    R.sup.1      Z        X    Hue                        __________________________________________________________________________     127                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                         --(CH.sub.2).sub.3 --                                                                    CN   reddish                                                                        blue                       128   "                  "             "       CONH.sub.2                                                                          blue                       129   "                  "             "       H    "                          130   "                (CH.sub.2).sub.3 OC.sub.4 H.sub.9                                                              "       CN   violet                     131                      "             "       "    red                            CH.sub.3 OC                                                                    ∥                                                                     O                                                                          132   "                (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                     "       "    "                          133                      "             "       "    bluish                                                                         red                        134    "               CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                           "       "    "                          135                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                         --(CH.sub.2).sub.2 --                                                                    CN   orange                     136   "                CH.sub.2 CH.sub.2 OCH.sub.3                                                                    "       "    "                          137   "                  "           --(CH.sub.2).sub.4 --                                                                    "    yellowish                                                                      red                        138   "                CH.sub.2 CH.sub.2 OH                                                                         --(CH.sub.2).sub.3 --                                                                    "    orange                     139   "                  "             "       H    red                        140   "                CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                              "       CN   orange                     141                    --(CH.sub.2).sub.3 --                                                                        CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        CN   orange                     142   "                  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              "    "                          143   "                  "           CH.sub.2 C.sub.2 C.sub.                                                                  " H.sub.5                                                                           "                          144                      "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              CONH.sub.2                                                                          red                        145   "                  "             "       H    "                          146   "                  "           CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     "    "                          147   "                  "             "       CONH.sub.2                                                                          "                          148                      "             "       "    bluish                                                                         red                        149   "                  "             "       H    "                          150   "                  "             "       CONH.sub.2                                                                          "                          151   "                  "           CH.sub.2 C.sub.2 --C.sub.6 H.sub.5                                                       "    "                          152                      "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              CN   yellowish                                                                      red                        153   "                  "           CH.sub.2 CH.sub. 2 CH.sub.2 OCH.sub.3                                                    "    "                          154                      "             "       "    "                          155   "                  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              "    "                          156                      "             "       "    red                        157   "                  "           CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     "    "                          158                    --(CH.sub.2).sub.3 --                                                                        CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CN   bluish                                                                         red                        159   "                  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              "    "                          160                      "             "       "    yellow                     161   "                  "           CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     "    "                          162                    --(CH.sub.2).sub.4 --                                                                          "       CN   red                        163   "                  "             "       CONH.sub.2                                                                          "                          164   "                  "             "       H    "                          165   "                --(CH.sub.2).sub.2 --                                                                        C.sub.4 H.sub.9 (n)                                                                      "    "                          166                    --(CH.sub.2).sub.4 --                                                                        CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CN   brown                      167   "                --(CH.sub.2).sub.3 --                                                                        H         "    yellow-                                                                        brown                      168                      "             "       "    yellow                     169                      "             "       "    orange                     170                      "             "       "    "                          171                     "              "       CN   red                        172                    --(CH.sub.2).sub.3 --                                                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                              CN   red                        173                      "             "       "    yellowish                                                                      red                        174                      "             "       "    "                                                               H.sub.5 C.sub.2                                                                |                                175                      "           (CH.sub.2).sub.3 OCH.sub.2 CH                                                            "    red                                                             |                                                                     (n)H.sub.9 C.sub.4                        176                      "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              H    orange                     177                      "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              CN   yellowish                                                                      red                        178                      "           (CH.sub.2).sub.6 OH                                                                      "    "                          179   "                  "           (CH.sub.2).sub.3 OCH.sub.3                                                               "    orange                     180                    --CH.sub.2 CH.sub.2 CH.sub.2 NCH.sub.2 CH.sub.2                                CH.sub.2      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CN   yellow                                            |                                                                     CH.sub.3                                                181                    --(CH.sub.2).sub.3 --                                                                          "       "    yellow-                                                                        ish red                    182   "                  "           (CH.sub.2).sub.2 CH.sub.2 OCOCH.sub.3                                                    "    yellow                     183                      "           (CH.sub.2).sub.6 OH                                                                      "    red                            C.sub.2 H.sub.5                                                                |                                                                     CH.sub.2 CHC.sub.4 H.sub.9 (n)                                             184                      "           CH.sub.2 CH.sub.2 OCH.sub.3                                                              "    orange                     185                      "             "       "    "                          186                      "           --(CH.sub.2).sub.3 OCH.sub.3                                                             "    reddish                                                                        yellow                     187   "                  "           C.sub.6 H.sub.5                                                                          "    orange                     188                      "           (CH.sub.2).sub.3 OCH.sub.3                                                               "    reddish                                                                        yellow                     189                      "             "       "    "                          __________________________________________________________________________

                                      Table 6                                      __________________________________________________________________________     No. D                  R.sup.1  R.sup.2  Z     Hue                             __________________________________________________________________________     190                    H        H        --(CH.sub.2).sub.3 --                                                                orange                          191   "                CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "     red                             192                    H        H        "     orange                          193   "                CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             "     red                             194                    H        H        "     "                               195   "                CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             "     "                               196                    (CH.sub.2).sub.3 OCH.sub.3                                                              H        "     red                             197 CH.sub.3 O--C        "      "        "     violet                              ∥                                                                     O                                                                          __________________________________________________________________________

EXAMPLE 198

29.5 parts of 2-aminobenzonitrile are dissolved in 800 parts by volume of water and 80 parts by volume of 30% strength hydrochloric acid at room temperature. 750 parts of ice are then added, followed, at from 0° to 5°C, by 77 parts by volume, added all at once, of a 23% strength sodium nitrite solution. After stirring for two hours at from 0° to 5°C, the following suspension is added to the clear or turbid diazonium salt solution: 66.0 parts of 2,6-bis-(β-methoxyethylamino)-3-cyano-4-methylpyridine are dissolved in 80 parts by volume of warm dimethylformamide, 12.5 parts of an adduct of about 23 moles of ethylene oxide to 1 mole of sperm oil alcohol are then added, and the solution is introduced into a mixture of 30 parts by volume of 30% strength hydrochloric acid and 1,000 parts by volume of water, whilst stirring.

About from 500 to 1,000 parts of ice are added to the coupling solution, followed by about 65 parts of 50% strength sodium hydroxide solution to bring the pH of the mixture to 2.5 - 3.2. After the coupling reaction has terminated, the mixture is warmed to 70°C and the product is filtered off and washed with hot water. After drying, about 97 to 98 parts of a yellow powder of the formula ##SPC29##

are obtained; the powder gives a yellow solution in dimethyl/formamide.

0.5 part of this dye are mixed thoroughly with 1,000 parts of polystyrene granules or powder by conventional processes. The mixture is then fused, which causes the dye to dissolve. The dye is stable in the melt at up to 300°C. After solidification, a deep yellow polystyrene of excellent fastness to light is obtained. The dye shows equal heat stability when incorporated into fused polyamide. The dye is also very suitable for the mass coloring of polypropylene, polyethylene, polyvinyl chloride or polyesters.

EXAMPLE 199

78 parts of 1-amino-2-trifluoromethyl-4-chlorobenzene are dissolved in 400 parts of 96% strength sulfuric acid at from 0 to 20°C. The mixture is cooled to from 0° to 4°C, 130 parts of 45% strength nitrosylsulfuric acid are added and the batch is stirred for 3 hours at from 0° to 5°C. It is then poured onto 1,200 parts of ice, whilst stirring, stirred for a further 30 minutes and filtered. After destroying excess nitrous acid, 117 parts of the coupling component of the formula ##SPC30##are added to the diazonium salt solution and the pH of the coupling solution is brought to from 2 to 3 by adding sodium hydroxide solution at from 0 to 5°C. After the coupling reaction has terminated, the dye of the formula ##SPC31##

which has precipitated is filtered off, washed with water and dried.

On coloring 1,000 parts of polystyrene with 0.5 part of this dye analogously to EXAMPLE 198, a yellow polystyrene of very good fastness to light is obtained.

                                      Table 7                                      __________________________________________________________________________     Exam-                                                                               R.sup.1       R.sup.2  R.sup.3                                                                           R.sup.4                                                                             R.sup.5                                                                           Hue                                     ple                                    of the mass-                            No.                                    colored                                                                        polystyrene                             __________________________________________________________________________     200 CH.sub.2 CH.sub.2 OCH.sub.3                                                                 (CH.sub.2).sub.2 OCH.sub.3                                                                C.sub.3 H.sub.7                                                                   CN   H  yellow                                  201  "           (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          "    "  "                                       202  "            "         "  "    Cl "                                       203  "           C.sub.2 H.sub.5                                                                           "  "    H  "                                       204  "           CH.sub.3   "  "    "  "                                       205  "           (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                      "  "    "  "                                       206 C.sub.2 H.sub.5                                                                             (CH.sub.2).sub.2 OCH.sub.3                                                                "  "    "  "                                       207 CH.sub.2 CH.sub.2 OH                                                                         "         "  "    "  "                                       208  "            "         "  CF.sub.3                                                                            "  "                                       209 CH.sub.2 CH.sub.2 OH                                                                        (CH.sub.2).sub.3 OCH.sub.3                                                                CH.sub.3                                                                          CF.sub.3                                                                            Cl "                                       210 C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                           "  CN   H  "                                       211  "            "         "  CF.sub.3                                                                            H  "                                       212  "            "         "  "    Cl "                                       213 C.sub.2 H.sub.5                                                                             CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                          CN   H  "                                       214  "           (CH.sub.2).sub.3 OH                                                                       "  "    "  "                                       215  "            "         "  CF.sub.3                                                                            Cl "                                       216 CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    H  "                                       217 C.sub.6 H.sub.5                                                                             H          "  "    "  "                                       218  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    "  "                                       219 C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                           "  COOCH.sub.3                                                                         "  "                                       220  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    "  "                                       221  "            "         "  "    Cl "                                       222 C.sub.4 H.sub.9 (n)                                                                          "         "  CN   "  "                                       223 (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                        (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                      "  CF.sub.3                                                                            H  "                                       224 C.sub.6 H.sub.13 (n)                                                                        CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                       225 H            C.sub.2 H.sub.5                                                                           "  CN   Cl "                                       226 "             "         C.sub.3 H.sub.7                                                                   "    "  "                                       227 "             "         "  CF.sub.3                                                                            H  "                                       228 "            CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          "    "  "                                       229 "             "         "  CN   "  "                                       230 "             "         "  COOCH.sub.3                                                                         Cl "                                       231 CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H          CH.sub.3                                                                          CN   H  "                                       232  "           "          "  CF.sub.3                                                                            H  "                                       233 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "  CN   H  "                                       234  "            "         H  SO.sub.2 C.sub.6 H.sub.5                                                            "  "                                       235 CH.sub.2 CH.sub.2 --C.sub.6 H.sub.5                                                         CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                          CN   "  "                                       236  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    "  "                                       237  "            "         C.sub.3 H.sub.7                                                                   "    "  "                                       238  "            "         CH.sub.3                                                                          "    Cl "                                       239  "           CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "  "    H  "                                       240  "           CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         "  "    "  "                                       241  "            "         "  "    Cl "                                       242 CH.sub.2 CH--O--C.sub.6 H.sub.5                                                             CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "  "    H  "                                           |                                                                     CH.sub.3                                                                   243 CH.sub.2 CH.sub. 2 CH.sub.2 OC.sub.6 H.sub.5                                                CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                       244 CH.sub.2 --CH--C.sub.6 H.sub.5                                                              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "  "    "  "                                           |-  OH                                                            245 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                   "         "  "    "  "                                       246  "           CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                       247 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                  CH.sub.2 --CH--CH.sub.3                                                                   CH.sub.3                                                                          CN   H  "                                                        |                                                                     OH                                                            248 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                        CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                       249 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                        "         "  "    "  "                                       250 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4 H.sub.9                                          "         "  "    "  "                                       251 C.sub.6 H.sub.5                                                                             CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "  "    "  yellow                                  252  "            "         "  "    Cl orange                                  253 C.sub.6 H.sub.4 CH.sub.3                                                                     "         "  "    H  "                                       254               "         "  "    "  yellow                                      CH.sub.3                                                                       |                                                                 255 --CH(CH.sub.2).sub.3 C--OH                                                                   "         "  "    "  "                                           ||                                                           CH.sub.3 CH.sub.3                                                          256              CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH                                                   "  "    "  "                                       257              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    "  "                                       258 CH.sub.2 CH.sub.2 OCH.sub.3                                                                  "         H  S0.sub.2 C.sub.6 H.sub.5                                                            "  "                                       259              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CH.sub.3                                                                          CN   "  "                                       260 (CH.sub.2).sub.3 OCHCH.sub.2 OCH.sub.3                                                       "         "  "    "  "                                           |                                                                     CH.sub.3                                                                   261 (CH.sub.2).sub.3 OCH.sub.2 CHOC.sub.6 H.sub.5                                               CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                           |                                                                     CH.sub.3                                                                   262 (CH.sub.2).sub.6 OH                                                                         CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CH.sub.3                                                                          CN   H  "                                       263 (CH.sub.2).sub.5 --CN                                                                        "         "  "    "  "                                       264 CH.sub.2 CH.sub.2 OCH.sub.3                                                                  "         C.sub.6 H.sub.5                                                                   "    "  "                                       265  "           CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  CF.sub.3                                                                            Cl "                                       266  "            "         H  "    "  "                                       267  "            "         C.sub.2 H.sub.5                                                                   CN   "  "                                       268 (CH.sub.2).sub.5 COOCH.sub.3                                                                 "         CH.sub.3                                                                          "    H  "                                       269 (CH.sub.2).sub.5 COOC.sub.2 H.sub.5                                                          "         "  "    "  "                                       270 (CH.sub.2).sub.5 COOC.sub.3 H.sub.7                                                          "         "  "    "  "                                       271 (CH.sub.2).sub.5 COOC.sub.4 H.sub.9                                                          "         "  "    "  "                                       272              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "  "    "  "                                       273 CH.sub.2 CH=CH.sub.2                                                                         "         "  "    "  "                                       274 CH.sub.2 CH=CH.sub.2                                                                        CH.sub.2 CH=CH.sub.2                                                                      "  "    "  "                                       275 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                               (CH.sub.2).sub.3 OCH.sub.3                                                                "  "    "  "                                       276 CH.sub.2 CH--C.sub.6 H.sub.5                                                                CH.sub.2 CH.sub.2 OH                                                                      "  "    "  "                                           |                                                                     CH.sub.3                                                                   277 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        SO.sub.2 CH.sub.3                                                                         "  "    "  "                                       278 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        COC.sub.6 H.sub.5                                                                         CH.sub.3                                                                          CN   H  yellow                                  279  "           SO.sub.2 C.sub.6 H.sub.5                                                                  "  "    "  "                                       280 CH.sub.2 CH.sub.2 OCH.sub.3                                                                  "         "  "    "  "                                       __________________________________________________________________________

                                      Table 8                                      __________________________________________________________________________     Exam-                                                                               R.sup.1      R.sup.2                                                                               R.sup.3                                                                             R.sup.4                                                                              R.sup.5                                                                           Hue                                     ple                                    of the mass-                            No.                                    colored                                                                        polystyrene                             __________________________________________________________________________     281 H           C.sub.2 H.sub.5                                                                         H    NO.sub.2                                                                             H  yellow                                  282 "           (CH.sub.2).sub.3 OCH.sub.3                                                              "    "     "  "                                       283 "           (CH.sub.2).sub.3 OCH(CH.sub.3 ).sub.2                                                   "    "     "  "                                       284 "           (CH.sub. 2).sub.3 OCH.sub.3                                                             CH.sub.3                                                                            "     "  orange                                  285 "            "       OCH.sub.3                                                                           "     "  red-orange                              286 C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                         "    "     "  scarlet                                 287  "           "       H    "     "  orange                                  288  "           "       CN   "     "  yellowish                                                                      red                                     289  "          C.sub.3 H.sub.7 (n)                                                                     "    "     "  "                                       290  "            "      "    "     C1 bluish red                              291  "          C.sub.2 H.sub.5                                                                         "    "     "  "                                       292 (CH.sub.2).sub.3 OCH.sub.3                                                                  "       "    "     "  "                                       293  "           "       "    "     "  yellowish                                                                      red                                     294 (CH.sub.2).sub.3 OCH.sub.3                                                                 C.sub.2 H.sub.5                                                                         Cl   NO.sub.2                                                                             H  yellowish                                                                      red                                     295 H            "       "    "     "  orange                                  296 "           (CH.sub.2).sub.3 OCH.sub.3                                                              "    "     "  "                                       297 "            "       NO.sub.2                                                                            "     "  red                                     298 C.sub.2 H.sub.5                                                                             "       "    "     "  bluish red                              299  "           "       CN   "     Br "                                       300 CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              C.sub.2 H.sub.5                                                                         "    H     H  yellow                                  301 C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2 OCOCH.sub.3                                                           "    "     "  "                                       302 CH.sub.2 CH.sub.2 OC.sub. 6 H.sub.5                                                        CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    Cl   NO.sub.2                                                                             "  orange                                  303  "           "       CN   "     "  Yellowish                                                                      red                                     304 CH.sub.2 CH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                                 "       "    "     "  scarlet                                 305  "           "       Cl   "     "  orange                                  306 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                  "       "    "     "  "                                       307 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                  "       CN   "     "  yellowish                                                                      red                                     308  "           "       "    "     Cl bluish red                              309  "           "       "    "     Br "                                       310  "          CH.sub.2 CH.sub.2 OH                                                                    "    "     "  "                                       311 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 CH.sub.2 CH.sub.2 OH                                                                    Cl   NO.sub.2                                                                             H  orange                                  312  "           "       CN   "     "  yellowish                                                                      red                                     313 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                         "       "    "     "  scarlet                                 314 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                        "       "    "     "  "                                       315  "           "       Cl   "     "  orange                                  316  "          CH.sub.2 CH.sub.2 OCH.sub.3                                                             "    "     "  "                                       317  "           "       CN   "     "  yellowish                                                                      red                                     318  "           "       NO.sub.2                                                                            "     "  red                                     319  "          CH.sub.2 CH.sub.2 OH                                                                    "    "     "  "                                       320  "           "       Br   "     "  red-orange                              321  "           "       COOCH.sub.3                                                                         "     "  "                                       322  "           "       H    "     "  orange                                  323  "           "       SO.sub.2 CH.sub.3                                                                   "     "  red                                     324  "           "       CH.sub.3                                                                            "     "  orange                                  325  "           "       OCH.sub.3                                                                           "     "  "                                       326  "           "       SO.sub.2 CH.sub.3                                                                   Cl    "  golden                                                                         yellow                                  327  "          CH.sub.2 CH.sub.2 OCH.sub.3                                                             CN   NO.sub.2                                                                             NO.sub.2                                                                          bluish red                              328  "           "       "    "     CN "                                       329  "           "       Cl   "     Cl yellow-                                                                        brown                                   330 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                       CH.sub.2 CH.sub.2 OCH.sub.3                                                             H    SO.sub.2 CH.sub.3                                                                    Cl yellow                                  331  "           "       Cl   "     H  "                                       332  "           "       Br   NO.sub.2                                                                             Br yellow-                                                                        brown                                   333  "          CH.sub.2 CH.sub.2 OH                                                                    COOCH.sub.3                                                                         Cl    Cl yellow                                  334  "           "       Cl   SO.sub.2 C.sub.6 H.sub.5                                                             H  "                                       335  "           "       CN   CN    "  orange                                  336  "           "       Cl   Cl    Cl yellow                                  337 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "    "     "  "                                       338  "           "       "    SO.sub.2 CH.sub.3                                                                    "  "                                       339  "           "       H    N=N--C.sub.6 H.sub.5                                                                 H  orange                                  340 CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.2 CH.sub.2 OCH.sub.3                                                             "    "     "  "                                       341  "           "       Cl   SO.sub.2 CH.sub.3                                                                    "  yellow                                  __________________________________________________________________________        proportions

                                      Table 9                                      __________________________________________________________________________     Exam-                                                                              D                  R.sup.1   R.sup.2   X  Hue                              ple                                           of the mass-                     No.                                           colored                                                                        polystyrene                      __________________________________________________________________________     342                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN  reddish                                                                        blue                             343   "                "         "        CONH.sub.2                                                                         blue                             344   "                "         "        H   "                                345   "              (CH.sub.2).sub.3 OC.sub.4 H.sub.9                                                        CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN  violet                           346                    "         "        "   red                              347   "              (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.                                                  "        "   "                                348                    "         "        "   bluish red                       349   "              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "   "                                350                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN  orange                           351   "              CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "   "                                352   "              C.sub.6 H.sub.5                                                                            "        "   yellowish red                    353   "              CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        CH.sub.2 CH.sub.2 OH                                                                      "   orange                           354   "                "         "        H   red                              355   "              CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         CN  orange                           356 CH.sub.3 OOCC.sub.2 H.sub.4 S                                                                     "         "        "   "                                357   "              CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "   "                                358   "              CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         "   "                                359                  CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CONH.sub.2                                                                         red                              360   "                "         "        H   "                                361   "              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "   "                                362   "                "         "        CONH.sub.2                                                                         "                                363                    "         "        "   bluish red                       364   "                "         "        H   "                                365                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 OH                                                                      CONH.sub.2                                                                         bluish red                       366   "              CH.sub.2 CH.sub.2 --C.sub.6 H.sub.5                                                        "        "   "                                367                  CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN  yellowish                                                                      red                              368   "              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "   scarlet                          369                    "         "        "   "                                370   "              CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "   "                                371                    "         "        "   red                              372   "              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "   "                                373                    "         "        "   bluish red                       374   "              CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "   "                                375                    "         "        "   yellow                           376   "              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "   "                                377                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN  red                              378   "                "         "        CONH.sub.2                                                                         "                                379   "                "         "        H   "                                380   "              C.sub.4 H.sub.9 (n)                                                                      C.sub.4 H.sub.9 (n)                                                                       "   "                                381                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN  brown                            382   "              H         (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3                                               "   yellow-                                                                        brown                            383                  H         H          "   yellow                           384                    "         "        "   orange                           385                    "         "        "   "                                386                    "         "        CN  red                              387                  CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN  red                              388                    "         "        "   yellowish                                                                      red                              389                    "       CH.sub.2 CH.sub.2 OH                                                                      "   scarlet                                               H.sub.5 C.sub.2                                                                |                                                390                  (CH.sub.2).sub.3 OCH.sub.2 CH                                                            (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                        "H  red                                                   |                                                                     (n)H.sub.9 C.sub.4                                        391                  H         H          H   orange                           392                  CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN  yellowish                                                                      red                              393                  (CH.sub.2).sub.6 OH                                                                      (CH.sub.2).sub.6 OH                                                                       "   "                                394   "              (CH.sub.2).sub.3 OCH.sub.3                                                               CH.sub.2 CH.sub. 2 OCCH.sub.3                                                             "   orange                                                          ∥                                                                     O                                               395                  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     CH.sub.2 CHOCOCH.sub.2 OC.sub.6 H.sub.5                                                   CN  yellow                           396   "                "         "        "   "                                397   "              (CH.sub.2).sub.2 CH.sub.2 OCOCH.sub.3                                                    (CH.sub.2).sub.2 CH.sub.2 OCOCH.sub.3                                                     "   "                                398                  (CH.sub.2).sub.6 OH                                                                      (CH.sub.2).sub.6 OH                                                                       "   red                                  C.sub.2 H.sub.5                                                                |                                                                     CH.sub.2 CHC.sub.4 H.sub.9 (n)                                             399                  CH.sub.2 CH.sub.2 OCH.sub.3                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               "   orange                           400                    "         "        "   "                                401                  --(CH.sub.2).sub.3 OCH.sub.3                                                             (CH.sub.2).sub.3 OCH.sub.3                                                                "   reddish                                                                        yellow                           402    "             C.sub.6 H.sub.5                                                                            "        "   orange                           403                  (CH.sub.2).sub.3 OCH.sub.3                                                                 "        "   reddish                                                                        yellow                           404                    "         "        "   "                                __________________________________________________________________________

                                      Table 10                                     __________________________________________________________________________     Exam-                                                                              D                   R.sup.1  R.sup.2                                                                               Hue                                    ple                                     of the mass-                           No.                                     colored                                                                        polystyrene                            __________________________________________________________________________     405                   H        H        orange                                 406 "                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    red                                    407                   H        H        orange                                 408 "                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             red                                    409                   H        H        "                                      410 "                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             "                                      __________________________________________________________________________

                                      Table 11                                     __________________________________________________________________________     Exam-                                                                          ple D                 R.sup.1  R.sup.2    R.sup.3                                                                             Hue                             No.                                                                            __________________________________________________________________________     411                 H        O.sub.4 H.sub.9 (n)                                                                         CH.sub.3                                                                            red                             412                 "        CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               413                 "        C.sub.6 H.sub.13 (n)                                                                        "    "                               414                 "        CH.sub.2 CH--C.sub.4 H.sub.9 (n)                                                            "    "                                                            |                                                                     C.sub.2 H.sub.5                                   415                 "                     "    "                               416                 "                     "    "                               417                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               418                   "        "          C.sub.3 H.sub.7 (r)                                                                 "                               419                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         CH.sub.3                                                                            "                               420                 C.sub.6 H.sub.13 (n)                                                                    C.sub.6 H.sub.13 (n)                                                                        "    "                               414                   "        "          "    "                               415                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         "    "                               416                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               417                 H          "          "    "                               418                 H        C.sub.4 H.sub.9 (n)                                                                         CH.sub.3                                                                            red                             419                 H          "          C.sub.3 H.sub.7 (n)                                                                 "                               420                 H        C.sub.6 H.sub.13 (n)                                                                        CH.sub.3                                                                            "                               421                 H        C.sub.4 H.sub.9 (n)                                                                         CH.sub.3                                                                            "                                   H.sub.3 COC                                                                    ∥                                                                     O                                                                          422                 H        CH.sub.2 --CH--C.sub.4 H.sub.9 (n)                                                          "    "                                                            |                                                                     C.sub.2 H.sub.5                                   423                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OH.sub.3                                                         "    ruby                            424                   "        "          C.sub.2 H.sub.                                                                      "                               425                   "      C.sub.4 H.sub.9 (n)                                                                         CH.sub.3                                                                            "                               426                 C.sub.4 H.sub.9 (n)                                                                       "          "    "                               427                 C.sub.6 H.sub.13 (n)                                                                    C.sub.6 H.sub.13 (n)                                                                        "    "                               428                 H        --CH.sub.2 --CH.sub.2 --CH.sub.2 --OCH.sub.3                                                CH.sub.3                                                                            red                             429                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "          CH.sub.3                                                                            ruby                            430                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         "    "                               431                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "    "                               432                   "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               433                 H        H            "    red                             434                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3                                                        CH.sub.3                                                                            ruby                                C.sub.2 H.sub.5 --CO                                                           ∥                                                                     O                                                                          435                 CH.sub.2 CH.sub. 2 OCH.sub.3                                                            CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "    "                               436                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         "    "                                   C.sub.17 H.sub.35 (n)                                                      437                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "    "                                   C.sub.2 H.sub.5 OC                                                             ∥                                                                     O                                                                          438                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               439                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "    yellow                          440                 CH.sub.2 CH.sub.2 OCH.sub.3                                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                                 "    yellow                          441                 "        "            C.sub.3 H.sub.7 (n)                                                                 "                               442                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        CH.sub.3                                                                            "                               443                 H        "            "    yellow                          444                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         "    golden                                                                         yellow                          445                 CH.sub.2 CH.sub.2 CH.sub. 2 OCH.sub.3                                                   C.sub.6 H.sub.5                                                                             "    orange                          446                 C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                         "    red-                                                                           orange                          447                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        "    "                               448                 "                     "    yellowish                                                                      red                             __________________________________________________________________________

EXAMPLE 449

29.5 parts of 2-aminobenzonitrile are dissolved in 800 parts by volume of water and 80 parts by volume of 30% strength hydrochloric acid at room temperature. 750 parts of ice are then added, followed, at from 0° to 5°C, by 77 parts by volume, added all at once, of a 23% strength sodium nitrite solution. After stirring for 2 hours at from 0° to 5°C, the following suspension is added to the clear or turbid diazonium salt solution: 65.5 parts of 2-N,N-diethylamino-3-cyano-4-methyl-6-methoxyethylaminopyridine are dissolved in 80 parts by volume of warm dimethylformamide, 12.5 parts of an addition product of about 23 moles of ethylene oxide to 1 mole of sperm oil alcohol and then added, and the solution is introduced into a mixture of 30 parts by volume of 30% strength hydrochloric acid and 1,000 parts by volume of water, whilst stirring.

About from 500 to 1,000 parts of ice are added to the coupling solution, followed by about 65 parts of 50% strength sodium hydroxide solution to bring the pH of the mixture to from 2.5 to 3.2. After the coupling reaction has terminated, the mixture is warmed to 60°C and the product is filtered off and washed with hot water. After drying, about 97 to 98 parts of a yellow powder of the formula ##SPC32##

are obtained; the powder gives a yellow solution in dimethyl/formamide.

0.5 part of this dye are mixed thoroughly with 1,000 parts of polystyrene granules or powder by conventional processes. The mixture is then fused, which causes the dye to dissolve. The dye is stable in the melt at up to 300°C. After solidification, a deep yellow polystyrene of excellent fastness to light is obtained. The dye shows equal heat stability when incorporated into fused polyamide. The mass colored polyamide is also very fast to light. The dye is also very suitable for the mass coloring of polypropylene, polyethylene, polyvinyl chloride and polyesters.

EXAMPLE 450

78 parts of 1-amino-2-trifluoromethyl-4-chlorobenzene are dissolved in 400 parts of 96% strength sulfuric acid at from 0° to 20°C. The mixture is cooled to from 0° to 4°C, 130 parts of 45% strength nitrosylsulfuric acid are added and the batch is stirred for 3 hours at from 0° to 5°C. The mixture is then poured onto 1,200 parts of ice, whilst stirring, stirred for a further 30 minutes and filtered. After destroying excess nitrous acid, 123 parts of the coupling component of the formula ##SPC33##

are added to the diazonium salt solution and the pH of the coupling solution is brought to from 2 to 3 by adding sodium hydroxide solution at from 0° to 5°C. After the coupling reaction has terminated, the dye of the formula ##SPC34##

which has precipitated is filtered off, washed with water and dried.

On coloring, 1,000 parts of polystyrene with 0.5 part of this dye analogously to Example 449, a yellow polystyrene of very good fastness to light is obtained.

The dyes characterized, in the table which follows, by their substituents, can also be used for mass coloration in the above manner, giving the hues shown in the table.

                                      Table 12                                     __________________________________________________________________________     Exam-                                                                              R.sup.1   R.sup.2     R.sup.3                                                                           R.sup.4                                                                             R.sup.5                                                                          Hue                                        ple                                 of the mass-                               No.                                 colored                                                                        polystyrene                                __________________________________________________________________________     451 N(C.sub.2 H.sub.5).sub.2                                                                 (CH.sub.2).sub.2 OCH.sub.3                                                                 C.sub.3 H.sub.7                                                                   CN   H yellow                                     452 "         (CH.sub.2).sub.3 OCH.sub.3                                                                 CH.sub.3                                                                          "    " "                                          453 "         "           "  "    Cl                                                                               "                                          454 "         C.sub.2 H.sub.5                                                                            "  "    H "                                          455 "         CH.sub.3    "  "    " "                                          456 "         (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                       "  "    " "                                          457 N(CH.sub.3).sub.2                                                                        (CH.sub.2).sub.2 OCH.sub.3                                                                 "  "    " "                                          458 N(C.sub.3 H.sub.7).sub.2                                                                 "           "  "    " "                                          459 "         "           "  CF.sub.3                                                                            " "                                          460 "         (CH.sub.2).sub.3 OCH.sub.3                                                                 CH.sub.3                                                                          CF.sub.3                                                                            Cl                                                                               "                                          461 N(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                            "  CN   H "                                          462           "           "  CF.sub.3                                                                            H "                                          463           "           "  "    Cl                                                                               "                                          464 N(CH.sub.3).sub.2                                                                        CH.sub.2 CH.sub.2 OH                                                                       "  CN   H "                                          465 "         (CH.sub.2).sub.3 OH                                                                        "  "    " "                                          466 "         "           "  CF.sub.3                                                                            Cl                                                                               "                                          467 N(C.sub.2 H.sub.5).sub.2                                                                 CH.sub.2 CH.sub.2 OCH.sub.3                                                                "  "    H "                                          468 N--C.sub.6 H.sub.5                                                                       H           "  "    " "                                              |                                                                     C.sub.2 H.sub.5                                                            469 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                "  "    " "                                          470 N(CH.sub.3).sub.2                                                                        C.sub.2 H.sub.5                                                                            "  COOCH.sub.3                                                                         " "                                          471 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                "  "    " "                                          472 "         "           "  "    Cl                                                                               "                                              CH.sub.2 OH                                                                473 N∠  "           "  CN   " "                                              C.sub.2 H.sub.5                                                            474 N(CH.sub.3).sub.2                                                                        (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                       "  CF.sub.3                                                                            H "                                          475 N(C.sub.4 H.sub.9).sub.2                                                                 CH.sub.2 CH.sub.2 OH                                                                       "  "    " "                                              C.sub.6 H.sub.5                                                            476 N∠  C.sub.2 H.sub.5                                                                            "  CN   Cl                                                                               "                                              CH.sub.2 CH.sub.2 OH                                                       477 "         "           C.sub.3 H.sub.7                                                                   "    " "                                          478 "         "           "  CF.sub.3                                                                            H "                                          479 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                CH.sub.3                                                                          "    " "                                          480 "         "           "  CN   " "                                          481 "         "           "  COOCH.sub.3                                                                         Cl                                                                               "                                          482 N(CH.sub.2 CH.sub.2 OCH.sub.3).sub.2                                                     H           "  CN   H "                                          483 "         "           "  CF.sub. 3                                                                           H "                                          484 "         CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "  CN   H "                                          485 "         "           H  SO.sub.2 C.sub.6 H.sub.5                                                            " "                                          486 "         CH.sub.2 CH.sub.2 OH                                                                       CH.sub.3                                                                          CN   " "                                          487 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                "  "    " "                                              CH.sub.2 CH.sub.3                                                          488 N∠  "           C.sub.3 H.sub.7                                                                   "    " "                                              C.sub.4 H.sub.9 (n)                                                        489 N[CH(CH.sub.3).sub.2 ].sub.2                                                             "           CH.sub.3                                                                          "    Cl                                                                               "                                          490 "         CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "  "    H "                                          491 "         CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                          "  "    " "                                              C.sub.2 H.sub.5                                                            492 N∠  "           "  "    Cl                                                                               "                                              C.sub.4 H.sub.9 (n)                                                        493 "         CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2                                                       "  "    H "                                          494 "         CH.sub.2 CH.sub.2 OH                                                                       "  "    " "                                          495 N CH.sub.2 CH(CH.sub.3).sub.2                                                            CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "  "    " "                                              CH.sub.2 CH.sub.2 CH.sub.3                                                     N∠                                                                   496 CH--CH.sub.2 CH.sub.2                                                                    "           "  "    " "                                              |                                                                     CH.sub.3                                                                   497 "         CH.sub.2 CH.sub.2 OH                                                                       "  "    " "                                          498 N(C.sub.2 H.sub.5).sub.2                                                                 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5                                                 "  "    " "                                          499 "         (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5                                       "  "    " "                                          500 "         (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH                                                      "  "    " "                                          501 "         (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OC.sub.4 H.sub.9                                        "  "    " "                                          502 "         C.sub.6 H.sub.5                                                                            "  "    " "                                          503 "         C.sub.6 H.sub.4 OCH.sub.3 (m)                                                              "  "    Cl                                                                               orange                                     504 "         C.sub.6 H.sub.4 CH.sub.3                                                                   "  "    H "                                          505 "                     "  "    " yellow                                                   CH.sub.3                                                                       |                                                       506 "         --CH(CH.sub.2).sub.3 C--OH                                                                 "  "    " "                                                        ||                                                           CH.sub.3 CH.sub.3                                                507 "                     "  "    " "                                          508 "                     "  "    " "                                          509 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                H  SO.sub.2 C.sub.6 H.sub.5                                                            " "                                          510 "                     CH.sub.3                                                                          CN   " "                                          511 "         (CH.sub.2).sub.3 OCHCH.sub.2 OCH.sub.3                                                     "  "    " "                                                        |                                                                     CH.sub.3                                                         512 "         (CH.sub.2).sub.3 OCH.sub.2 CHOC.sub.6 H.sub.5                                              "  "    " "                                                        |                                                                     CH.sub.3                                                         513 "         (CH.sub.2).sub.6 OH                                                                        "  "    " "                                          514 "         (CH.sub.2).sub.5 --CN                                                                      "  "    " "                                          515 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                                C.sub.6 H.sub.5                                                                   "    " "                                          516 "         "           "  CF.sub.3                                                                            Cl                                                                               "                                          517 "         "           H  "    " "                                          518 "         "           C.sub.2 H.sub.5                                                                   CN   " "                                          519 "         (CH.sub.2).sub.5 COOCH.sub.3                                                               CH.sub.3                                                                          "    H "                                          520 "         (CH.sub.2).sub.5 COOC.sub.2 H.sub.5                                                        "  "    " "                                          521 "         (CH.sub.2).sub.5 COOC.sub.3 H.sub.7                                                        "  "    " "                                          522 "         (CH.sub.2).sub.5 COOC.sub.4 H.sub.9                                                        "  "    " "                                          523 "         CH.sub.2 CH.sub.2--                                                                        "  "    " "                                          524 "         CH.sub.2 CH=CH.sub.2                                                                       "  "    " "                                          525 N(CH.sub.3).sub.2                                                                        CH.sub.2 CH=CH.sub.2                                                                       "  "    " "                                          526 N(C.sub.2 H.sub.5).sub.2                                                                 CH.sub.2 CH.sub.2 CH.sub.2 OH                                                              "  "    " "                                          527 "         CH.sub.2 CH--C.sub.6 H.sub.5                                                               "  "    " "                                                        |                                                                     CH.sub.3                                                         528 N(CHCH.sub.2 CH.sub.3).sub.2                                                             CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                       "  "    " "                                              |                                                                     CH.sub.3                                                                   529 N(C.sub.2 H.sub.5).sub.2                                                                 COC.sub.6 H.sub.5                                                                          CH.sub.3                                                                          CN   H "                                          530 "         SO.sub.2 C.sub.6 H.sub.5                                                                   "  "    " "                                          531 N(C.sub.3 H.sub.7).sub.2                                                                 "           "  "    " "                                          __________________________________________________________________________

                                      Table 13                                     __________________________________________________________________________     Exam-                                                                              R.sup.1   R.sup.2  R.sup.3                                                                             R.sup.4                                                                              R.sup.5                                                                           Hue                                       ple                                  of the mass-                              No.                                  colored                                                                        polystyrene                               __________________________________________________________________________     532 N(C.sub.2 H.sub.5).sub.2                                                                 C.sub.2 H.sub.5                                                                         H    NO.sub.2                                                                             H  yellow                                    533 "         (CH.sub.2).sub.3 OCH.sub.3                                                              "    "     "  "                                         534 "         (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2                                                    "    "     "  "                                         535 "         (CH.sub.2).sub.3 OCH.sub.3                                                              CH.sub.3                                                                            "     "  orange                                    536 "         "        OCH.sub.3                                                                           "     "  red-                                                                           orange                                    537 "         C.sub.2 H.sub.5                                                                         "    "     "  yellowish                                                                      red                                       538 "         "        H    "     "  orange                                    539 "         "        CN   "     "  yellowish                                                                      red                                       540 "         C.sub.3 H.sub.7 (n)                                                                     "    "     "  scarlet                                   541 "         "        "    "     Cl bluish                                                                         red                                       542 "         C.sub.2 H.sub.5                                                                         "    "     "  "                                         543 N(C.sub.3 H.sub.7).sub.2                                                                 "        "    "     "  "                                         544 N(C.sub.4 H.sub.9).sub.2                                                                 "        "    "     "  yellowish                                                                      red                                       545 N(C.sub.2 H.sub.5).sub.2                                                                 "        Cl   "     H  "                                         546 N(C.sub.3 H.sub.7).sub.2                                                                 "        "    "     "  orange                                    547 "         (CH.sub.2).sub.3 OCH.sub.3                                                              "    "     "  "                                         548 "         "        NO.sub.2                                                                            "     "  red                                       549 N(C.sub.3 H.sub.5).sub.2                                                                 "        "    "     "  bluish red                                550 "         "        CN   "     Br "                                         551 N(CH.sub.2 CH.sub.2 OCCH.sub.3).sub.2                                                    C.sub.2 H.sub.5                                                                         "    H     H  yellow                                        ∥                                                                     O                                                                          552 "         CH.sub.2 CH.sub.2 OCOCH.sub.3                                                           "    "     "  "                                         553 N(C.sub.2 H.sub.5).sub.2                                                                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    Cl   NO.sub.2                                                                             "  orange                                    554 "         "        CN   "     "  yellowish                                                                      red                                       555 N(C.sub.4 H.sub.9).sub.2                                                                 "        "    "     "  scarlet                                   556 "         "        Cl   "     "  orange                                    557 "         "        Br   "     "  "                                         558 "         "        CN   "     "  yellowish                                                                      red                                       559 "         "        "    "     Cl bluish red                                560 "         "        "    "     Br "                                         561 "         CH.sub.2 CH.sub.2 OH                                                                    "    "     "  "                                         562 N(C.sub.2 H.sub.5).sub.2                                                                 (CH.sub.2).sub.3 OC.sub.2 H.sub.5                                                       Cl   "     H  orange                                    563 "         "        CN   "     "  yellowish                                                                      red                                       564 N(CH.sub.2 CH.sub.2 OCH.sub.3).sub.2                                                     "        "    "     "  "                                         565 N(CH.sub.3).sub.2                                                                        "        "    "     "  "                                         566 N(C.sub.3 H.sub.7).sub.2                                                                 "        Cl   "     "  orange                                    567 "         (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                       "    "     "  "                                         568 "         "        CN   "     "  yellowish                                                                      red                                       569 "         "        NO.sub.2                                                                            "     "  red                                       570 N(C.sub.2 H.sub.5).sub.2                                                                 "        "    "     "  "                                         571 "         "        Br   "     "  red-orange                                572 "         "        COOCH.sub.3                                                                         "     "  "                                         573 "         "        H    "     "  orange                                    574 "         "        SO.sub.2 CH.sub.3                                                                   "     "  red                                       575 "         "        CH.sub.3                                                                            "     "  orange                                    576 "         "        OCH.sub.3                                                                           "     "  "                                         577 "         "        SO.sub.2 CH.sub.3                                                                   Cl    "  yellow                                    578 "         "        CN   NO.sub.2                                                                             NO.sub.2                                                                          bluish                                                                         red                                       579 "         "        "    "     CN "                                         580 "         "        Cl   "     Cl yellow-                                                                        brown                                     581 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                             H    SO.sub.2 CH.sub.3                                                                    "  yellow                                    582 "         "        Cl   "     H  "                                         583 "         "        Br   NO.sub.2                                                                             Br yellow-                                                                        brown                                     584 "         CH.sub.2 CH.sub.2 OH                                                                    COOCH.sub.3                                                                         Cl    Cl yellow                                    585 "         "        Cl   SO.sub.2 C.sub.6 H.sub.5                                                             H  "                                         586 "         "        CN   CN    "  orange                                    587 "         "        Cl   Cl    Cl yellow                                    588 N(C.sub.3 H.sub.7).sub.2                                                                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    "    "     "  "                                         589 "         "        "    SO.sub.2 CH.sub.3                                                                    "  "                                         590 "         "        H    N=N--C.sub.6 H.sub.5                                                                 H  orange                                    591 "         CH.sub.2 CH.sub.2 OCH.sub.3                                                             "    "     "  "                                         592 N(C.sub.2 H.sub.5).sub.2                                                                 "        Cl   SO.sub.2 CH.sub.3                                                                    "  yellow                                    __________________________________________________________________________

                                      Table 14                                     __________________________________________________________________________     Exam-                                                                              D                 R.sup.1                                                                               R.sup.2    X     Hue of                           ple                                           the mass-                        No.                                           colored                                                                        polystyrene                      __________________________________________________________________________     593                   N(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN    reddish                                                                        blue                             594 "                 "      "          CONH.sub.2                                                                           blue                             595 "                 "      "          H      "                               596 "                 "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN    violet                           597                          "          "     red                                  CH.sub.3 OC                                                                    ∥                                                                     O                                                                          598 "                 N(C.sub.3 H.sub.7).sub.2                                                              "          "      "                               599                   "      "          "     bluish red                       600 "                 N(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "      "                               601                   "      "          "     orange                           602 "                 "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "      "                               603 "                 N(C.sub.3 H.sub.7).sub.2                                                              "          "     yellowish red                    604 "                 "      CH.sub.2 CH.sub.2 OH                                                                      "     orange                           605 "                 "      "          H     red                              606 "                 "      CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         CN    orange                               CH.sub.3 OOCC.sub.2 H.sub.4 S                                              607                   "      "          "      "                               608 "                 "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "      "                               609 "                 "      CH.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                         "      "                               610                   "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               CONH.sub.2                                                                           red                              611 "                 "      "          H      "                               612 "                 N(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "      "                               613 "                 "      "          CONH.sub.2                                                                            "                               614                   "      "          "     bluish                                                                         red                              615 "                 "      "          H      "                               616                   "      CH.sub.2 CH.sub.2 OH                                                                      CONH.sub.2                                                                            "                               617 "                 N(CH.sub.3).sub.2                                                                     "          "      "                                618                  N(C.sub.2 H.sub.5).sub.2                                                              CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN    yellowish red                                                                  scarlet                          619 "                 "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "                                      620                   "      "          "      "                               621 "                 "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "      "                               622                   "      "          "     red                              623 "                 "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "      "                               624                   "      "          "     bluish                                                                         red                              625 "                 "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "      "                               626                   "      "          "     yellow                           627 "                 "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "      "                               628                   "      "          "     red                              629 "                 "      "          CONH.sub.2                                                                           "                                630 "                 "      "          H      "                               631 "                 "      C.sub.4 H.sub.9 (n)                                                                       "      "                               632                   "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      CN    brown                            633 "                 "      (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3                                               "     yellow-                                                                        brown                            634                   "      H          "     yellow                           635                   "      "          "     orange                           636                   "      "          "      "                               637                   "      "          "     red                              638                   "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "      "                               639                   "      "          "     yellowish red                    640                   "      CH.sub.2 CH.sub.2 OH                                                                      "     scarlet                          641                          (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OH                                                     "     red                              642                   "      H          H     orange                           643                   "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               CN    yellowish red                    644                   "      (CH.sub.2).sub.6 OH                                                                       "     scarlet                          645 "                 "      CH.sub.2 CH.sub.2 OCCH.sub.3                                                              "     orange                                                        ∥                                                                     O                                                 646                          CH.sub.2 CHOCOCH.sub.2 OC.sub.6 H.sub.5                                                   "     yellow                           647 "                 NO     "          "      "                               648 "                 "      (CH.sub.2).sub.2 CH.sub.2 OCOCH.sub.3                                                     "      "                               649                          (CH.sub.2).sub.6 OH                                                                       "     red                                  C.sub.2 H.sub.5                                                                |                                                                     CH.sub.2 CHC.sub.4 H.sub.9                                                 650                   NO     CH.sub.2 CH.sub.2 OCH.sub.3                                                               "     orange                           651                   "      "          "      "                               652                          (CH.sub.2).sub.3 OCH.sub.3                                                                "     reddish                                                                        yellow                           653 "                        "          "     orange                           654                   "      "          "     reddish                                                                        yellow                           655                   "      "          "      "                               __________________________________________________________________________

                                      Table 15                                     __________________________________________________________________________                                        Hue of                                      Exam-                              the mass-                                   ple                                colored                                     No. D             R.sup.1                                                                               R.sup.2   polystyrene                                 __________________________________________________________________________     656                      H         orange                                      657 "             "      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     red                                         658               "      H         orange                                      659 "             NN--H  CH.sub.2 CH.sub.2 OCH.sub.3                                                              red                                         660               N(C.sub.2 H.sub.5).sub.2                                                              H          "                                          661 "             "      CH.sub.2 CH.sub.2 OCH.sub.3                                                               "                                          662               "      "          "                                          __________________________________________________________________________

                                      Table 16                                     __________________________________________________________________________     Exam-                                                                          ple                                                                            No. D                  R.sup.1   R.sup.2    Hue                                __________________________________________________________________________                                     C.sub.2 H.sub.5                                663                   CH.sub.2 CH.sub.2 OCH.sub.3                                                              N∠    ruby                                                               C.sub.2 H.sub.5                                664 "                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "           "                                 665 "                 C.sub.4 H.sub.9 (n)                                                                       "           "                                 666 "                 H          "          red                                667 "                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                                 ruby                               668                   "         N(C.sub.2 H.sub.5).sub.2                                                                    "                                 669 "                 "         N(CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3).su                                     b.2          "                                 670 "                 CH.sub.2 CH.sub.2 OCH.sub.3                                                              N(CH.sub.2 CH.sub.2 OCH.sub.3).sub.2                                                        "                                 671 "                 C.sub.4 H.sub.9 (n)                                                                      N(C.sub.4 H.sub.9 (n)).sub.2                                                                "                                 672                   "         N(C.sub.2 H.sub.5).sub.2                                                                   red                                673 "                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      "           "                                 674 "                 CH.sub.2 CH.sub.2 OCH.sub.3                                                               "           "                                 675 "                 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     N(CH.sub.2 CH.sub.2 OCH.sub.3).sub.2                                                        "                                 676                   CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                     N(C.sub.2 H.sub.5).sub.2                                                                   red                                677 "                 C.sub.4 H.sub.9 (n)                                                                       "           "                                 678                   C.sub.4 H.sub.9 (n)   red-                                                                           orange                             __________________________________________________________________________ 

We claim:
 1. A thermoplastic resinous material which has been colored by mixing with a dye and distributing the dye homogeneously in the melt, said dye having the formula ##SPC35##wherein A¹ is A or ##SPC36## D¹ is thienyl substituted by cyano, C₁ - to C₃ -alkyl, C₁₇ H₃₅, phenyl or C₁ - to C₈ -alkoxycarbonyl; R¹ is hydrogen or alkyl of 1 to 3 carbon atoms; X is hydrogen, carbamoyl or cyano; A is hydrogen; C₁ to C₈ -alkyl; C₂ - to C₈ -alkyl substituted by hydroxy, OCHO, OCOCH₃, OCOC₂ H₅, OCOC₃ H₇, C₂ - to C₄ -hydroxyalkoxy, cyano, C₁ - to C₈ -alkoxy, C₁ - to C₈ -alkoxycarbonyl, phenoxy or phenyl; cyclohexyl; methylcyclohexyl; norbornyl; phenyl; β-hydroxy-β-phenylethyl; or (CH₂)₃ (OC₂ H₄)_(m) OT; m is 1 or 2; T is C₁ - to C₄ -alkyl, benzyl or phenyl; ##EQU19## is pyrrolidino, piperidino, morpholino, hexamethyleneimino piperazino, N-methylpiperazino or N-β-hydroxyethylpiperazino and Z is C₂ - to C₈ -alkylene, --, --, ).sub. ##EQU20## --(CH₂)₃ --N--(CH₂)₃, --(CH₂)₃ --OC₂ H₄ --O--(CH₂)₃, --(CH₂)₃ --O--(CH₂)₄ O (CH₂) ₃ --, ##SPC37##
 2. A thermoplastic resinous material according to claim 1 containing as the dye a compound of the formula in claim 1, wherein X is cyano and R¹ is methyl.
 3. A thermoplastic resinous material according to claim 1 containing as the dye a compound of the formula in claim 1, whereinA is hydrogen, C₁ - to C₈ -alkyl, C₁ - to C₈ -alkoxy, substituted C₂ - or C₃ -alkyl, phenoxyethyl, phenoxypropyl, cyclohexyl, methylcyclohexyl, norbornyl, phenyl-C₁ - to C₄ -alkyl or phenyl and A¹ is A.
 4. A thermoplastic resinous material according to claim 1 containing as the dye a compound of the formula in claim 1, wherein Z is C₂ - to C₆ -alkylene, ##EQU21## ##SPC38##
 5. Thermoplastic resinous material according to claim 1 containing the dye of the formula ##SPC39##
 6. A thermoplastic resinous material according to claim 1 colored with 0.01 to 1% of the dye according to the formula in claim
 1. 7. A thermoplastic resinous material according to claim 1 wherein said material is polystyrene, a polyamide, polyethylene, polypropylene, a polyester, a polycarbonate or polyvinyl chloride. 